Installation issue with `pipx` on macOS?

Description

I'm a long-time Poetry-enthusiast ❤️ Amazing project and kudos to the whole team, thanks for all you do! 🎉 🌮 🍰

Since I have a workaround, I'm not terribly worried about this issue. That said, if it helps someone else I'm happy to provide a workaround & some information.

My workflow is basically:

# Install homebrew
brew install pipx
pipx install poetry
# Use poetry

Also, note that I have multiple versions of Python installed:

brew list | grep python
python-argcomplete
python-build
python-certifi
python-packaging
python-setuptools
python@3.10
python@3.11
python@3.12
python@3.9

Workarounds

The workaround, which solves this issue for me is exactly as yene stated here: https://github.com/python-poetry/poetry/issues/6841#issuecomment-1978245754

ln -s /opt/homebrew/bin/python3 /opt/homebrew/bin/python

Poetry Installation Method

pipx

Operating System

macOS 14.4

Poetry Version

Poetry (version 1.8.2)

Poetry Configuration

Configuration file exists at /Users/me/Library/Preferences/pypoetry, reusing this directory.

Consider moving TOML configuration files to /Users/me/Library/Application Support/pypoetry, as support for the legacy directory will be removed in an upcoming release.
cache-dir = "/Users/me/Library/Caches/pypoetry"
experimental.system-git-client = false
installer.max-workers = null
installer.modern-installation = true
installer.no-binary = null
installer.parallel = true
keyring.enabled = true
solver.lazy-wheel = true
virtualenvs.create = true
virtualenvs.in-project = true
virtualenvs.options.always-copy = false
virtualenvs.options.no-pip = false
virtualenvs.options.no-setuptools = false
virtualenvs.options.system-site-packages = false
virtualenvs.path = "{cache-dir}/virtualenvs"  # /Users/me/Library/Caches/pypoetry/virtualenvs
virtualenvs.prefer-active-python = true
virtualenvs.prompt = "{project_name}-py{python_version}"
warnings.export = true

Python Sysconfig

Platform: "macosx-14.0-arm64"
Python version: "3.11"
Current installation scheme: "venv"

Paths: 
        data = "/Users/me/Desktop/github/myjob/myproj/.venv"
        include = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/include/python3.11"
        platinclude = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/include/python3.11"
        platlib = "/Users/me/Desktop/github/myjob/myproj/.venv/lib/python3.11/site-packages"
        platstdlib = "/Users/me/Desktop/github/myjob/myproj/.venv/lib/python3.11"
        purelib = "/Users/me/Desktop/github/myjob/myproj/.venv/lib/python3.11/site-packages"
        scripts = "/Users/me/Desktop/github/myjob/myproj/.venv/bin"
        stdlib = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib/python3.11"

Variables: 
        ABIFLAGS = ""
        AC_APPLE_UNIVERSAL_BUILD = "0"
        AIX_BUILDDATE = "0"
        AIX_GENUINE_CPLUSPLUS = "0"
        ALIGNOF_LONG = "8"
        ALIGNOF_SIZE_T = "8"
        ALT_SOABI = "0"
        ANDROID_API_LEVEL = "0"
        AR = "/usr/bin/xcrun ar"
        ARFLAGS = "rcs"
        BASECFLAGS = "-Wsign-compare -Wunreachable-code -fno-common -dynamic"
        BASECPPFLAGS = ""
        BASEMODLIBS = ""
        BINDIR = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/bin"
        BINLIBDEST = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib/python3.11"
        BLDLIBRARY = ""
        BLDSHARED = "clang -bundle -undefined dynamic_lookup -isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk"
        BOOTSTRAP_HEADERS = "\"
        BUILDEXE = ".exe"
        BUILDPYTHON = "python.exe"
        BUILD_GNU_TYPE = "aarch64-apple-darwin23.4.0"
        BYTESTR_DEPS = "\"
        CC = "clang"
        CCSHARED = ""
        CFLAGS = "-Wsign-compare -Wunreachable-code -fno-common -dynamic -DNDEBUG -g -fwrapv -O3 -Wall -isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk"
        CFLAGSFORSHARED = ""
        CFLAGS_ALIASING = "-fno-strict-aliasing"
        CONFIGFILES = "configure configure.ac acconfig.h pyconfig.h.in Makefile.pre.in"
        CONFIGURE_CFLAGS = "-isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk"
        CONFIGURE_CFLAGS_NODIST = "-I/opt/homebrew/include -flto -std=c11 -Wextra -Wno-unused-parameter -Wno-missing-field-initializers -Wstrict-prototypes -Werror=implicit-function-declaration -fvisibility=hidden"
        CONFIGURE_CPPFLAGS = "-I/opt/homebrew/include"
        CONFIGURE_LDFLAGS = "-isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk"
        CONFIGURE_LDFLAGS_NODIST = "-L/opt/homebrew/lib -Wl,-rpath,/opt/homebrew/lib -flto -Wl,-export_dynamic -g"
        CONFIGURE_LDFLAGS_NOLTO = "-flto=thin"
        CONFIG_ARGS = "'--prefix=/opt/homebrew/opt/python@3.11' '--enable-ipv6' '--datarootdir=/opt/homebrew/opt/python@3.11/share' '--datadir=/opt/homebrew/opt/python@3.11/share' '--without-ensurepip' '--enable-loadable-sqlite-extensions' '--with-openssl=/opt/homebrew/opt/openssl@3' '--enable-optimizations' '--with-system-expat' '--with-system-libmpdec' '--with-readline=editline' '--with-lto' '--enable-framework=/opt/homebrew/opt/python@3.11/Frameworks' '--with-dtrace' '--with-dbmliborder=ndbm' 'MACOSX_DEPLOYMENT_TARGET=14' 'CFLAGS=-isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk' 'CFLAGS_NODIST=-I/opt/homebrew/include' 'LDFLAGS=-isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk' 'LDFLAGS_NODIST=-L/opt/homebrew/lib -Wl,-rpath,/opt/homebrew/lib' 'CPPFLAGS=-I/opt/homebrew/include' 'py_cv_module__tkinter=disabled' 'PKG_CONFIG_PATH=/opt/homebrew/opt/mpdecimal/lib/pkgconfig:/opt/homebrew/opt/openssl@3/lib/pkgconfig:/opt/homebrew/opt/readline/lib/pkgconfig:/opt/homebrew/opt/sqlite/lib/pkgconfig:/opt/homebrew/opt/xz/lib/pkgconfig' 'PKG_CONFIG_LIBDIR=/usr/lib/pkgconfig:/opt/homebrew/Library/Homebrew/os/mac/pkgconfig/14' 'CC=clang'"
        CONFINCLUDEDIR = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/include"
        CONFINCLUDEPY = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/include/python3.11"
        COREPYTHONPATH = ""
        COVERAGE_INFO = "/private/tmp/pythonA3.11-20240402-4978-3ygh5v/Python-3.11.9/coverage.info"
        COVERAGE_LCOV_OPTIONS = "--rc lcov_branch_coverage=1"
        COVERAGE_REPORT = "/private/tmp/pythonA3.11-20240402-4978-3ygh5v/Python-3.11.9/lcov-report"
        COVERAGE_REPORT_OPTIONS = "--rc lcov_branch_coverage=1 --branch-coverage --title "CPython 3.11 LCOV report [commit $(shell )]""
        CPPFLAGS = "-I. -I./Include -I/opt/homebrew/include"
        CXX = "clang++"
        DECIMAL_CFLAGS = "-DCONFIG_64=1 -DANSI=1 -DHAVE_UINT128_T=1"
        DECIMAL_LDFLAGS = "-lmpdec"
        DEEPFREEZE_C = "Python/deepfreeze/deepfreeze.c"
        DEEPFREEZE_DEPS = "./Tools/scripts/deepfreeze.py _bootstrap_python ./Programs/_freeze_module.py \"
        DEEPFREEZE_OBJS = "Python/deepfreeze/deepfreeze.o"
        DESTDIRS = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11 /opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib /opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib/python3.11 /opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib/python3.11/lib-dynload"
        DESTLIB = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib/python3.11"
        DESTPATH = ""
        DESTSHARED = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib/python3.11/lib-dynload"
        DFLAGS = ""
        DIRMODE = "755"
        DIST = "README.rst ChangeLog configure configure.ac acconfig.h pyconfig.h.in Makefile.pre.in Include Lib Misc Ext-dummy"
        DISTDIRS = "Include Lib Misc Ext-dummy"
        DISTFILES = "README.rst ChangeLog configure configure.ac acconfig.h pyconfig.h.in Makefile.pre.in"
        DLINCLDIR = "."
        DLLLIBRARY = ""
        DOUBLE_IS_ARM_MIXED_ENDIAN_IEEE754 = "0"
        DOUBLE_IS_BIG_ENDIAN_IEEE754 = "0"
        DOUBLE_IS_LITTLE_ENDIAN_IEEE754 = "1"
        DTRACE = "/usr/sbin/dtrace"
        DTRACE_DEPS = "\"
        DTRACE_HEADERS = "Include/pydtrace_probes.h"
        DTRACE_OBJS = ""
        DYNLOADFILE = "dynload_shlib.o"
        ENABLE_IPV6 = "1"
        ENSUREPIP = "no"
        EXE = ""
        EXEMODE = "755"
        EXPAT_CFLAGS = ""
        EXPAT_LDFLAGS = "-lexpat"
        EXPORTSFROM = ""
        EXPORTSYMS = ""
        EXTRATESTOPTS = ""
        EXTRA_CFLAGS = ""
        EXT_SUFFIX = ".cpython-311-darwin.so"
        FILEMODE = "644"
        FLOAT_WORDS_BIGENDIAN = "0"
        FREEZE_MODULE = "./_bootstrap_python ./Programs/_freeze_module.py"
        FREEZE_MODULE_BOOTSTRAP = "./Programs/_freeze_module"
        FREEZE_MODULE_BOOTSTRAP_DEPS = "Programs/_freeze_module"
        FREEZE_MODULE_DEPS = "_bootstrap_python ./Programs/_freeze_module.py"
        FROZEN_FILES_IN = "\"
        FROZEN_FILES_OUT = "\"
        GETPGRP_HAVE_ARG = "0"
        GITBRANCH = ""
        GITTAG = ""
        GITVERSION = ""
        GNULD = "no"
        HAVE_ACCEPT = "1"
        HAVE_ACCEPT4 = "0"
        HAVE_ACOSH = "1"
        HAVE_ADDRINFO = "1"
        HAVE_ALARM = "1"
        HAVE_ALIGNED_REQUIRED = "0"
        HAVE_ALLOCA_H = "1"
        HAVE_ALTZONE = "0"
        HAVE_ASINH = "1"
        HAVE_ASM_TYPES_H = "0"
        HAVE_ATANH = "1"
        HAVE_BIND = "1"
        HAVE_BIND_TEXTDOMAIN_CODESET = "0"
        HAVE_BLUETOOTH_BLUETOOTH_H = "0"
        HAVE_BLUETOOTH_H = "0"
        HAVE_BROKEN_MBSTOWCS = "0"
        HAVE_BROKEN_NICE = "0"
        HAVE_BROKEN_PIPE_BUF = "0"
        HAVE_BROKEN_POLL = "0"
        HAVE_BROKEN_POSIX_SEMAPHORES = "0"
        HAVE_BROKEN_PTHREAD_SIGMASK = "0"
        HAVE_BROKEN_SEM_GETVALUE = "1"
        HAVE_BROKEN_UNSETENV = "0"
        HAVE_BUILTIN_ATOMIC = "1"
        HAVE_BZLIB_H = "1"
        HAVE_CHFLAGS = "1"
        HAVE_CHMOD = "1"
        HAVE_CHOWN = "1"
        HAVE_CHROOT = "1"
        HAVE_CLOCK = "1"
        HAVE_CLOCK_GETRES = "1"
        HAVE_CLOCK_GETTIME = "1"
        HAVE_CLOCK_NANOSLEEP = "0"
        HAVE_CLOCK_SETTIME = "1"
        HAVE_CLOSE_RANGE = "0"
        HAVE_COMPUTED_GOTOS = "1"
        HAVE_CONFSTR = "1"
        HAVE_CONIO_H = "0"
        HAVE_CONNECT = "1"
        HAVE_COPY_FILE_RANGE = "0"
        HAVE_CRYPT_H = "0"
        HAVE_CRYPT_R = "0"
        HAVE_CTERMID = "1"
        HAVE_CTERMID_R = "1"
        HAVE_CURSES_FILTER = "1"
        HAVE_CURSES_H = "1"
        HAVE_CURSES_HAS_KEY = "1"
        HAVE_CURSES_IMMEDOK = "1"
        HAVE_CURSES_IS_PAD = "1"
        HAVE_CURSES_IS_TERM_RESIZED = "1"
        HAVE_CURSES_RESIZETERM = "1"
        HAVE_CURSES_RESIZE_TERM = "1"
        HAVE_CURSES_SYNCOK = "1"
        HAVE_CURSES_TYPEAHEAD = "1"
        HAVE_CURSES_USE_ENV = "1"
        HAVE_CURSES_WCHGAT = "1"
        HAVE_DB_H = "1"
        HAVE_DECL_RTLD_DEEPBIND = "0"
        HAVE_DECL_RTLD_GLOBAL = "1"
        HAVE_DECL_RTLD_LAZY = "1"
        HAVE_DECL_RTLD_LOCAL = "1"
        HAVE_DECL_RTLD_MEMBER = "0"
        HAVE_DECL_RTLD_NODELETE = "1"
        HAVE_DECL_RTLD_NOLOAD = "1"
        HAVE_DECL_RTLD_NOW = "1"
        HAVE_DECL_TZNAME = "0"
        HAVE_DEVICE_MACROS = "1"
        HAVE_DEV_PTC = "0"
        HAVE_DEV_PTMX = "1"
        HAVE_DIRECT_H = "0"
        HAVE_DIRENT_D_TYPE = "1"
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        HAVE_DUP3 = "0"
        HAVE_DYLD_SHARED_CACHE_CONTAINS_PATH = "1"
        HAVE_DYNAMIC_LOADING = "1"
        HAVE_ENDIAN_H = "0"
        HAVE_EPOLL = "0"
        HAVE_EPOLL_CREATE1 = "0"
        HAVE_ERF = "1"
        HAVE_ERFC = "1"
        HAVE_ERRNO_H = "1"
        HAVE_EVENTFD = "0"
        HAVE_EXECV = "1"
        HAVE_EXPLICIT_BZERO = "0"
        HAVE_EXPLICIT_MEMSET = "0"
        HAVE_EXPM1 = "1"
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        HAVE_FDOPENDIR = "1"
        HAVE_FDWALK = "0"
        HAVE_FEXECVE = "0"
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        HAVE_FSEEKO = "1"
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        HAVE_FTELLO = "1"
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        HAVE_FTRUNCATE = "1"
        HAVE_FUTIMENS = "1"
        HAVE_FUTIMES = "1"
        HAVE_FUTIMESAT = "0"
        HAVE_GAI_STRERROR = "1"
        HAVE_GCC_ASM_FOR_MC68881 = "0"
        HAVE_GCC_ASM_FOR_X64 = "0"
        HAVE_GCC_ASM_FOR_X87 = "0"
        HAVE_GCC_UINT128_T = "1"
        HAVE_GDBM_DASH_NDBM_H = "0"
        HAVE_GDBM_H = "0"
        HAVE_GDBM_NDBM_H = "0"
        HAVE_GETADDRINFO = "1"
        HAVE_GETC_UNLOCKED = "1"
        HAVE_GETEGID = "1"
        HAVE_GETENTROPY = "1"
        HAVE_GETEUID = "1"
        HAVE_GETGID = "1"
        HAVE_GETGRGID = "1"
        HAVE_GETGRGID_R = "1"
        HAVE_GETGRNAM_R = "1"
        HAVE_GETGROUPLIST = "1"
        HAVE_GETGROUPS = "1"
        HAVE_GETHOSTBYADDR = "1"
        HAVE_GETHOSTBYNAME = "1"
        HAVE_GETHOSTBYNAME_R = "0"
        HAVE_GETHOSTBYNAME_R_3_ARG = "0"
        HAVE_GETHOSTBYNAME_R_5_ARG = "0"
        HAVE_GETHOSTBYNAME_R_6_ARG = "0"
        HAVE_GETHOSTNAME = "1"
        HAVE_GETITIMER = "1"
        HAVE_GETLOADAVG = "1"
        HAVE_GETLOGIN = "1"
        HAVE_GETNAMEINFO = "1"
        HAVE_GETPAGESIZE = "1"
        HAVE_GETPEERNAME = "1"
        HAVE_GETPGID = "1"
        HAVE_GETPGRP = "1"
        HAVE_GETPID = "1"
        HAVE_GETPPID = "1"
        HAVE_GETPRIORITY = "1"
        HAVE_GETPROTOBYNAME = "1"
        HAVE_GETPWENT = "1"
        HAVE_GETPWNAM_R = "1"
        HAVE_GETPWUID = "1"
        HAVE_GETPWUID_R = "1"
        HAVE_GETRANDOM = "0"
        HAVE_GETRANDOM_SYSCALL = "0"
        HAVE_GETRESGID = "0"
        HAVE_GETRESUID = "0"
        HAVE_GETRUSAGE = "1"
        HAVE_GETSERVBYNAME = "1"
        HAVE_GETSERVBYPORT = "1"
        HAVE_GETSID = "1"
        HAVE_GETSOCKNAME = "1"
        HAVE_GETSPENT = "0"
        HAVE_GETSPNAM = "0"
        HAVE_GETUID = "1"
        HAVE_GETWD = "1"
        HAVE_GLIBC_MEMMOVE_BUG = "0"
        HAVE_GRP_H = "1"
        HAVE_HSTRERROR = "1"
        HAVE_HTOLE64 = "0"
        HAVE_IEEEFP_H = "0"
        HAVE_IF_NAMEINDEX = "1"
        HAVE_INET_ATON = "1"
        HAVE_INET_NTOA = "1"
        HAVE_INET_PTON = "1"
        HAVE_INITGROUPS = "1"
        HAVE_INTTYPES_H = "1"
        HAVE_IO_H = "0"
        HAVE_IPA_PURE_CONST_BUG = "0"
        HAVE_KILL = "1"
        HAVE_KILLPG = "1"
        HAVE_KQUEUE = "1"
        HAVE_LANGINFO_H = "1"
        HAVE_LARGEFILE_SUPPORT = "0"
        HAVE_LCHFLAGS = "1"
        HAVE_LCHMOD = "1"
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        HAVE_LIBNDBM = "0"
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        HAVE_LINUX_CAN_J1939_H = "0"
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        HAVE_LINUX_MEMFD_H = "0"
        HAVE_LINUX_NETLINK_H = "0"
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        HAVE_NETPACKET_PACKET_H = "0"
        HAVE_NET_IF_H = "1"
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        PY_CFLAGS_NODIST = "-I/opt/homebrew/include -flto -std=c11 -Wextra -Wno-unused-parameter -Wno-missing-field-initializers -Wstrict-prototypes -Werror=implicit-function-declaration -fvisibility=hidden -fprofile-instr-use=code.profclangd -I./Include/internal"
        PY_COERCE_C_LOCALE = "1"
        PY_CORE_CFLAGS = "-Wsign-compare -Wunreachable-code -fno-common -dynamic -DNDEBUG -g -fwrapv -O3 -Wall -isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk -I/opt/homebrew/include -flto -std=c11 -Wextra -Wno-unused-parameter -Wno-missing-field-initializers -Wstrict-prototypes -Werror=implicit-function-declaration -fvisibility=hidden -fprofile-instr-use=code.profclangd -I./Include/internal -I. -I./Include -I/opt/homebrew/include -DPy_BUILD_CORE"
        PY_CORE_LDFLAGS = "-isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk -L/opt/homebrew/lib -Wl,-rpath,/opt/homebrew/lib -flto -Wl,-export_dynamic -g"
        PY_CPPFLAGS = "-I. -I./Include -I/opt/homebrew/include"
        PY_ENABLE_SHARED = "0"
        PY_FORMAT_SIZE_T = ""z""
        PY_LDFLAGS = "-isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk"
        PY_LDFLAGS_NODIST = "-L/opt/homebrew/lib -Wl,-rpath,/opt/homebrew/lib -flto -Wl,-export_dynamic -g"
        PY_LDFLAGS_NOLTO = "-isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk -flto=thin"
        PY_SQLITE_ENABLE_LOAD_EXTENSION = "1"
        PY_SQLITE_HAVE_SERIALIZE = "1"
        PY_SSL_DEFAULT_CIPHERS = "1"
        PY_SSL_DEFAULT_CIPHER_STRING = "0"
        PY_STDMODULE_CFLAGS = "-Wsign-compare -Wunreachable-code -fno-common -dynamic -DNDEBUG -g -fwrapv -O3 -Wall -isysroot /Library/Developer/CommandLineTools/SDKs/MacOSX14.sdk -I/opt/homebrew/include -flto -std=c11 -Wextra -Wno-unused-parameter -Wno-missing-field-initializers -Wstrict-prototypes -Werror=implicit-function-declaration -fvisibility=hidden -fprofile-instr-use=code.profclangd -I./Include/internal -I. -I./Include -I/opt/homebrew/include"
        PY_SUPPORT_TIER = "2"
        Py_DEBUG = "0"
        Py_ENABLE_SHARED = "0"
        Py_HASH_ALGORITHM = "0"
        Py_STATS = "0"
        Py_SUNOS_VERSION = "0"
        Py_TRACE_REFS = "0"
        QUICKTESTOPTS = "-x test_subprocess test_io test_lib2to3 \"
        READELF = ":"
        RESSRCDIR = "Mac/Resources/framework"
        RETSIGTYPE = "void"
        RUNSHARED = "DYLD_FRAMEWORK_PATH=/private/tmp/pythonA3.11-20240402-4978-3ygh5v/Python-3.11.9"
        SCRIPTDIR = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib"
        SETPGRP_HAVE_ARG = "0"
        SHELL = "/bin/sh"
        SHLIBS = "-ldl  -framework CoreFoundation"
        SHLIB_SUFFIX = ".so"
        SIGNED_RIGHT_SHIFT_ZERO_FILLS = "0"
        SITEPATH = ""
        SIZEOF_DOUBLE = "8"
        SIZEOF_FLOAT = "4"
        SIZEOF_FPOS_T = "8"
        SIZEOF_INT = "4"
        SIZEOF_LONG = "8"
        SIZEOF_LONG_DOUBLE = "8"
        SIZEOF_LONG_LONG = "8"
        SIZEOF_OFF_T = "8"
        SIZEOF_PID_T = "4"
        SIZEOF_PTHREAD_KEY_T = "8"
        SIZEOF_PTHREAD_T = "8"
        SIZEOF_SHORT = "2"
        SIZEOF_SIZE_T = "8"
        SIZEOF_TIME_T = "8"
        SIZEOF_UINTPTR_T = "8"
        SIZEOF_VOID_P = "8"
        SIZEOF_WCHAR_T = "4"
        SIZEOF__BOOL = "1"
        SOABI = "cpython-311-darwin"
        SRCDIRS = "Modules   Modules/_blake2   Modules/_ctypes   Modules/_decimal   Modules/_decimal/libmpdec   Modules/_io   Modules/_multiprocessing   Modules/_sha3   Modules/_sqlite   Modules/_sre   Modules/_xxtestfuzz   Modules/cjkcodecs   Modules/expat   Objects   Parser   Programs   Python   Python/frozen_modules   Python/deepfreeze"
        SRC_GDB_HOOKS = "./Tools/gdb/libpython.py"
        STATIC_LIBPYTHON = "1"
        STDC_HEADERS = "1"
        STRICT_SYSV_CURSES = "/* Don't use ncurses extensions */"
        STRIPFLAG = "-s"
        SUBDIRS = ""
        SUBDIRSTOO = "Include Lib Misc"
        SYSLIBS = ""
        SYS_SELECT_WITH_SYS_TIME = "1"
        TESTOPTS = ""
        TESTPATH = ""
        TESTPYTHON = "DYLD_FRAMEWORK_PATH=/private/tmp/pythonA3.11-20240402-4978-3ygh5v/Python-3.11.9 ./python.exe -E"
        TESTPYTHONOPTS = ""
        TESTRUNNER = "DYLD_FRAMEWORK_PATH=/private/tmp/pythonA3.11-20240402-4978-3ygh5v/Python-3.11.9 ./python.exe -E ./Tools/scripts/run_tests.py"
        TESTSUBDIRS = "ctypes/test \"
        TESTTIMEOUT = "1200"
        TEST_MODULES = "yes"
        THREAD_STACK_SIZE = "0x1000000"
        TIMEMODULE_LIB = "0"
        TIME_WITH_SYS_TIME = "1"
        TM_IN_SYS_TIME = "0"
        TZPATH = "/usr/share/zoneinfo:/usr/lib/zoneinfo:/usr/share/lib/zoneinfo:/etc/zoneinfo"
        UNICODE_DEPS = "\"
        UNIVERSALSDK = ""
        UPDATE_FILE = "./Tools/scripts/update_file.py"
        USE_COMPUTED_GOTOS = "0"
        VERSION = "3.11"
        WASM_ASSETS_DIR = "./opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11"
        WASM_STDLIB = "./opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11/lib/python3.11/os.py"
        WHEEL_PKG_DIR = ""
        WINDOW_HAS_FLAGS = "1"
        WITH_DECIMAL_CONTEXTVAR = "1"
        WITH_DOC_STRINGS = "1"
        WITH_DTRACE = "1"
        WITH_DYLD = "1"
        WITH_EDITLINE = "1"
        WITH_FREELISTS = "1"
        WITH_LIBINTL = "0"
        WITH_NEXT_FRAMEWORK = "1"
        WITH_PYMALLOC = "1"
        WITH_VALGRIND = "0"
        X87_DOUBLE_ROUNDING = "0"
        XMLLIBSUBDIRS = "xml xml/dom xml/etree xml/parsers xml/sax"
        abiflags = ""
        abs_builddir = "/private/tmp/pythonA3.11-20240402-4978-3ygh5v/Python-3.11.9"
        abs_srcdir = "/private/tmp/pythonA3.11-20240402-4978-3ygh5v/Python-3.11.9"
        base = "/Users/me/Desktop/github/myjob/myproj/.venv"
        datarootdir = "/opt/homebrew/opt/python@3.11/share"
        exec_prefix = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11"
        installed_base = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11"
        installed_platbase = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11"
        platbase = "/Users/me/Desktop/github/myjob/myproj/.venv"
        platlibdir = "lib"
        prefix = "/opt/homebrew/opt/python@3.11/Frameworks/Python.framework/Versions/3.11"
        projectbase = "/opt/homebrew/Cellar/python@3.11/3.11.9/bin"
        py_version = "3.11.9"
        py_version_nodot = "311"
        py_version_nodot_plat = ""
        py_version_short = "3.11"
        srcdir = "/opt/homebrew/Cellar/python@3.11/3.11.9/Frameworks/Python.framework/Versions/3.11/lib/python3.11/config-3.11-darwin"
        userbase = "/Users/me/Library/Python/3.11"

Example pyproject.toml

[tool.poetry]
name = "myproj"
version = "0.1.0"
description = ""
authors = ["b-long <b-long@users.noreply.github.com>"]

[tool.poetry.dependencies]
python = ">=3.11,<3.12"
requests = "^2.31.0"


[build-system]
requires = ["poetry-core>=1.0.0"]
build-backend = "poetry.core.masonry.api"

Poetry Runtime Logs

Without `-vvv`: 


$ poetry install 
Configuration file exists at /Users/me/Library/Preferences/pypoetry, reusing this directory.

Consider moving TOML configuration files to /Users/me/Library/Application Support/pypoetry, as support for the legacy directory will be removed in an upcoming release.

[Errno 2] No such file or directory: 'python'

With -vvv:

myproj-py3.11brian:myproj me$ poetry install -vvv
Configuration file exists at /Users/me/Library/Preferences/pypoetry, reusing this directory.

Consider moving TOML configuration files to /Users/me/Library/Application Support/pypoetry, as support for the legacy directory will be removed in an upcoming release.
Loading configuration file /Users/me/Library/Preferences/pypoetry/config.toml
Loading configuration file /Users/me/Desktop/github/myjob/myproj/poetry.toml
Trying to detect current active python executable as specified in the config.
Unable to detect the current active python executable. Falling back to default.

  Stack trace:

  18  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/cleo/application.py:327 in run
       325│ 
       326│             try:
     → 327│                 exit_code = self._run(io)
       328│             except BrokenPipeError:
       329│                 # If we are piped to another process, it may close early and send a

  17  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/console/application.py:190 in _run
       188│         self._load_plugins(io)
       189│ 
     → 190│         exit_code: int = super()._run(io)
       191│         return exit_code
       192│ 

  16  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/cleo/application.py:431 in _run
       429│             io.input.interactive(interactive)
       430│ 
     → 431│         exit_code = self._run_command(command, io)
       432│         self._running_command = None
       433│ 

  15  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/cleo/application.py:473 in _run_command
       471│ 
       472│         if error is not None:
     → 473│             raise error
       474│ 
       475│         return terminate_event.exit_code

  14  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/cleo/application.py:454 in _run_command
       452│ 
       453│         try:
     → 454│             self._event_dispatcher.dispatch(command_event, COMMAND)
       455│ 
       456│             if command_event.command_should_run():

  13  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/cleo/events/event_dispatcher.py:26 in dispatch
        24│ 
        25│         if listeners:
     →  26│             self._do_dispatch(listeners, event_name, event)
        27│ 
        28│         return event

  12  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/cleo/events/event_dispatcher.py:85 in _do_dispatch
        83│                 break
        84│ 
     →  85│             listener(event, event_name, self)
        86│ 
        87│     def _sort_listeners(self, event_name: str) -> None:

  11  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/console/application.py:299 in configure_env
       297│ 
       298│         env_manager = EnvManager(poetry, io=io)
     → 299│         env = env_manager.create_venv()
       300│ 
       301│         if env.is_venv() and io.is_verbose():

  10  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/utils/env/env_manager.py:443 in create_venv
       441│ 
       442│         cwd = self._poetry.file.path.parent
     → 443│         env = self.get(reload=True)
       444│ 
       445│         if not env.is_sane():

   9  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/utils/env/env_manager.py:324 in get
       322│             base_prefix = self.get_base_prefix()
       323│ 
     → 324│         return VirtualEnv(prefix, base_prefix)
       325│ 
       326│     def list(self, name: str | None = None) -> list[VirtualEnv]:

   8  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/utils/env/virtual_env.py:44 in __init__
        42│         # from inside the virtualenv.
        43│         if base is None:
     →  44│             output = self.run_python_script(GET_BASE_PREFIX)
        45│             self._base = Path(output.strip())
        46│ 

   7  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/utils/env/base_env.py:313 in run_python_script
       311│ 
       312│     def run_python_script(self, content: str, **kwargs: Any) -> str:
     → 313│         return self.run(
       314│             self._executable,
       315│             "-I",

   6  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/utils/env/base_env.py:305 in run
       303│     def run(self, bin: str, *args: str, **kwargs: Any) -> str:
       304│         cmd = self.get_command_from_bin(bin) + list(args)
     → 305│         return self._run(cmd, **kwargs)
       306│ 
       307│     def run_pip(self, *args: str, **kwargs: Any) -> str:

   5  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/utils/env/virtual_env.py:88 in _run
        86│     def _run(self, cmd: list[str], **kwargs: Any) -> str:
        87│         kwargs["env"] = self.get_temp_environ(environ=kwargs.get("env"))
     →  88│         return super()._run(cmd, **kwargs)
        89│ 
        90│     def get_temp_environ(

   4  ~/.local/pipx/venvs/poetry/lib/python3.12/site-packages/poetry/utils/env/base_env.py:338 in _run
       336│                 output = ""
       337│             else:
     → 338│                 output = subprocess.check_output(
       339│                     cmd, stderr=stderr, env=env, text=True, **kwargs
       340│                 )

   3  /opt/homebrew/Cellar/python@3.12/3.12.3/Frameworks/Python.framework/Versions/3.12/lib/python3.12/subprocess.py:466 in check_output
        464│         kwargs['input'] = empty
        465│ 
     →  466│     return run(*popenargs, stdout=PIPE, timeout=timeout, check=True,
        467│                **kwargs).stdout
        468│ 

   2  /opt/homebrew/Cellar/python@3.12/3.12.3/Frameworks/Python.framework/Versions/3.12/lib/python3.12/subprocess.py:548 in run
        546│         kwargs['stderr'] = PIPE
        547│ 
     →  548│     with Popen(*popenargs, **kwargs) as process:
        549│         try:
        550│             stdout, stderr = process.communicate(input, timeout=timeout)

   1  /opt/homebrew/Cellar/python@3.12/3.12.3/Frameworks/Python.framework/Versions/3.12/lib/python3.12/subprocess.py:1026 in __init__
       1024│                             encoding=encoding, errors=errors)
       1025│ 
     → 1026│             self._execute_child(args, executable, preexec_fn, close_fds,
       1027│                                 pass_fds, cwd, env,
       1028│                                 startupinfo, creationflags, shell,

  FileNotFoundError

  [Errno 2] No such file or directory: 'python'

  at /opt/homebrew/Cellar/python@3.12/3.12.3/Frameworks/Python.framework/Versions/3.12/lib/python3.12/subprocess.py:1955 in _execute_child
      1951│                         err_filename = orig_executable
      1952│                     if errno_num != 0:
      1953│                         err_msg = os.strerror(errno_num)
      1954│                     if err_filename is not None:
    → 1955│                         raise child_exception_type(errno_num, err_msg, err_filename)
      1956│                     else:
      1957│                         raise child_exception_type(errno_num, err_msg)
      1958│                 raise child_exception_type(err_msg)

Start by reproducing the documented Homebrew and pipx installation workflow on macOS 14.4 with multiple Python versions, using the supplied Python sysconfig and the linked workaround as comparison points. The issue is done when the installation failure is isolated and either fixed or clearly documented with a reliable supported installation path.